But sure as heck not impossible, it just takes a commitment to learning a very complex detailed facet of business and regulations. 

Here is some info: SF STR FAQAssuming the info is up-to-date, it must be your permanent residence (you must live at the property for a minimum 275 days a year), you can rent unhosted a max of 90 nights a year, you need a business license, and you need to pay the city $925 for a STR certificate.

Short-term rentals can be a great starting point, especially in markets with high tourism or business travel.

That said, I've seen many of these carriers are pulling away from habitation exposures (non-renewing a good portion of that business).  

I am looking to network and build a strong business relationship with a local real estate agent.

"Chasing" after a tenant is not good business and will waste a ton of your time.

From what Ive read, it looks like I may have to get a business certificate to do this in SF but Im not sure what that entails or what else is involved?

This is a business purpose loan and will have a prepayment penalty and possibly cost a bit more than conventional financing.

He had a tech job and we talked the business and he was legit and when meeting the family, they were very respectful. 

I live in Detroit but envision running the investment as a business, not a third job: Pay top dollar for the best PMC.